There are three settings we need to embed in this field. The first is to tell it what kind of numbering we want to do (in this case, “First, Second, Third”), what case we want to use (upper case, title case, etc.), and a switch to tell Microsoft Word to increment the numbers. Click each of these settings as shown below, being sure to click Add to Field after each one:
Warning  Making even minor changes to an outline numbering scheme won't necessarily change the initial position you've selected in the gallery, but rather may create a new gallery position, overwriting an existing one. Because of this problem, attaching numbering to styles is strongly recommended. This is covered in greater detail later in this chapter and in the chapter on Styles.

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Each section within an InDesign document can be numbered differently. This allows you to use one type of numerals to consecutively number a document's preface or other introductory materials and another numeral system for the remainder of the document. You must first define your document's sections, and then you can add section markers or page markers to your master pages. Apply the master page to document pages to include the section and page numbers on the document pages.
One of the harder things to do in Adobe InDesign, surprisingly for a page layout tool, is to create multilevel or outline format numbered lists.  The right way to accomplish this, according to the folks at Adobe, is to create a Style for every level of the list you’d like to have! Here are Adobe’s instructions on how to do so (This content is taken directly from https://helpx.adobe.com/indesign/using/bullets-numbering.html#create_multi_level_lists):

See Word's Numbering Explained by John McGhie, MVP - comprehensive and not pretty (Downloadable pdf file in letter size) - Reading this is vital to anyone attempting to use automatic numbering or bullets in a law office setting or other places where the documents are likely to be reused or heavily edited. See also How to Create a Template with a downloadable template with style-based numbering.
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